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No_Go, what makes you think this guy is interested? Everything I read seems like he's interested in the effect he has over her rather than interested in her.
Very sexy and very pretty
What a beautiful girl
P.S. If it makes you feel any better, my nickname for my fiance is
like this one too, Dakota, right?
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In regards to her one on one lunches with her boss, I settled with: I want her to do whatever makes her happy but I wanted to warn her that "work spouse syndrome" is a real thing, and even though she may go to lunch or dinner with innocent intentions, she's giving her male boss who clearly likes her many opportunities one on one to build emotional rapport by doing so many one on one lunches and coffee runs together.